KINGSWAY FINANCIAL SERVICES INC — Insider Transactions
Form 4 filings by directors, officers, and 10%+ shareholders
SEC rules require corporate insiders — including directors, executive officers, and any shareholder owning more than 10% of a company's shares — to report changes in their ownership within two business days of a transaction. These disclosures are filed as Form 4. Open-market purchases (code P) are generally considered the most meaningful signal, as insiders are spending their own money.
| Insider | Title | Type | Shares | Price | Value | Owns After | Date |
|---|---|---|---|---|---|---|---|
| Hansen Kent A | CFO & EVP | Tax Withholding | 3,565 | $12.83 | $45,739 | 125,285 | Dec 29, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Sale | 30,000 | $13.32 | $399,600 | 1,459,534 | Dec 23, 2025 |
| Stilwell Value LLC | — | Sale | 19,229 | $12.80 | $246,131 | 300,000 | Dec 22, 2025 |
| Stilwell Activist Fund, L.P. | — | X | 218,842 | $8.25 | $1,805,447 | 371,568 | Dec 17, 2025 |
| OAKMONT CAPITAL INC | — | X | 500,000 | $8.25 | $4,125,000 | 1,987,830 | Dec 17, 2025 |
| Kavanagh Terence Michael | — | X | 500,000 | $8.25 | $4,125,000 | 1,987,830 | Dec 17, 2025 |
| Hannon Gregory Paul | — | X | 500,000 | $8.25 | $4,125,000 | 1,987,830 | Dec 17, 2025 |
| Patinkin Adam Jonathan | — | X | 540,000 | $8.25 | $4,455,000 | 1,024,000 | Dec 17, 2025 |
| Horowitz Joshua | — | X | 252,500 | $8.25 | $2,083,125 | 367,500 | Dec 17, 2025 |
| Hansen Kent A | CFO & EVP | Purchase | 122 | $12.82 | $1,564 | 136,472 | Dec 16, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Purchase | 195 | $12.82 | $2,500 | 1,489,534 | Dec 16, 2025 |
| Stilwell Associates, L.P. | — | Sale | 34,269 | $12.80 | $438,643 | 545,135 | Dec 16, 2025 |
| Stilwell Activist Fund, L.P. | — | Sale | 67,500 | $12.80 | $864,000 | 579,404 | Dec 11, 2025 |
| Stilwell Activist Fund, L.P. | — | Sale | 20,000 | $12.80 | $256,000 | 646,904 | Dec 8, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Purchase | 192 | $13.03 | $2,502 | 1,489,339 | Nov 28, 2025 |
| Hansen Kent A | CFO & EVP | Purchase | 120 | $13.03 | $1,564 | 136,350 | Nov 28, 2025 |
| Hansen Kent A | CFO & EVP | Purchase | 123 | $12.70 | $1,562 | 136,230 | Nov 17, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Purchase | 197 | $12.70 | $2,502 | 1,489,147 | Nov 17, 2025 |
| Hansen Kent A | CFO & EVP | Purchase | 111 | $14.08 | $1,563 | 136,107 | Oct 30, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Purchase | 177 | $14.08 | $2,492 | 1,488,950 | Oct 30, 2025 |
| Hansen Kent A | CFO & EVP | Purchase | 98 | $15.92 | $1,560 | 135,996 | Oct 15, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Purchase | 157 | $15.92 | $2,499 | 1,488,773 | Oct 15, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Purchase | 171 | $14.63 | $2,502 | 1,488,616 | Sep 30, 2025 |
| Hansen Kent A | CFO & EVP | Purchase | 107 | $14.63 | $1,565 | 135,898 | Sep 30, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Other | 14,100 | $14.57 | $205,437 | 34,100 | Sep 26, 2025 |
| Stilwell Value Partners VII, L.P. | — | Sale | 5,953 | $14.40 | $85,723 | 604,698 | Sep 16, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Purchase | 174 | $14.36 | $2,499 | 1,530,745 | Sep 15, 2025 |
| Hansen Kent A | CFO & EVP | Purchase | 109 | $14.36 | $1,565 | 135,791 | Sep 15, 2025 |
| Stilwell Joseph | — | Sale | 14,944 | $14.41 | $215,343 | 3,590,980 | Sep 8, 2025 |
| Hansen Kent A | CFO & EVP | Purchase | 107 | $14.49 | $1,550 | 135,682 | Aug 29, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Purchase | 173 | $14.49 | $2,507 | 1,530,571 | Aug 29, 2025 |
| Stilwell Activist Fund, L.P. | — | Sale | 7,642 | $14.18 | $108,364 | 466,893 | Aug 22, 2025 |
| STILWELL ASSOCIATES L P | — | Sale | 12,123 | $13.95 | $169,116 | 650,152 | Aug 18, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Purchase | 176 | $14.16 | $2,492 | 1,530,398 | Aug 18, 2025 |
| Hansen Kent A | CFO & EVP | Purchase | 111 | $14.16 | $1,572 | 135,575 | Aug 18, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Purchase | 174 | $14.42 | $2,509 | 1,530,222 | Jul 30, 2025 |
| Hansen Kent A | CFO & EVP | Purchase | 108 | $14.42 | $1,557 | 135,464 | Jul 30, 2025 |
| Hansen Kent A | CFO & EVP | Purchase | 108 | $14.49 | $1,565 | 135,356 | Jul 15, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Purchase | 172 | $14.49 | $2,492 | 1,530,048 | Jul 15, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Purchase | 179 | $14.02 | $2,510 | 1,529,876 | Jul 1, 2025 |
| Hansen Kent A | CFO & EVP | Purchase | 111 | $14.02 | $1,556 | 135,248 | Jul 1, 2025 |
| Stilwell Value Partners VII, L.P. | — | Sale | 5,896 | $13.90 | $81,954 | 481,817 | Jun 27, 2025 |
| Hansen Kent A | CFO & EVP | Purchase | 114 | $13.77 | $1,570 | 135,137 | Jun 13, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Purchase | 181 | $13.77 | $2,492 | 1,529,697 | Jun 13, 2025 |
| Hansen Kent A | CFO & EVP | Purchase | 24 | $12.82 | $308 | 135,023 | May 30, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Purchase | 195 | $12.82 | $2,500 | 1,529,516 | May 30, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Purchase | 247 | $10.12 | $2,500 | 1,529,321 | May 15, 2025 |
| Hansen Kent A | CFO & EVP | Purchase | 31 | $10.12 | $314 | 134,999 | May 15, 2025 |
| Hansen Kent A | CFO & EVP | Purchase | 36 | $8.71 | $314 | 134,968 | Apr 30, 2025 |
| Fitzgerald John Taylor Maloney | President and CEO | Purchase | 287 | $8.71 | $2,500 | 1,529,074 | Apr 30, 2025 |